CA2280109C - Compositions de revetements aqueux, preparation et utilisation de ces produits dans la fabrication de vernis-laques au four - Google Patents

Compositions de revetements aqueux, preparation et utilisation de ces produits dans la fabrication de vernis-laques au four Download PDF

Info

Publication number: CA2280109C
Authority: CA; Canada
Prior art keywords: component; aqueous dispersion; carbon atoms; polyester; aliphatic
Prior art date: 1998-08-17
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA 2280109

Other languages

English (en)

Other versions

CA2280109A1 (fr

Inventor

Christoph Irle

Harald Blum

Joachim Petzoldt

Heino Muller

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-08-17

Filing date

1999-08-12

Publication date

2007-07-24

1998-08-17 Priority claimed from DE1998137062 external-priority patent/DE19837062A1/de

1998-08-17 Priority claimed from DE1998137063 external-priority patent/DE19837063A1/de

1999-08-12 Application filed by Bayer AG filed Critical Bayer AG

2000-02-17 Publication of CA2280109A1 publication Critical patent/CA2280109A1/fr

2007-07-24 Application granted granted Critical

2007-07-24 Publication of CA2280109C publication Critical patent/CA2280109C/fr

2019-08-12 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000004922 lacquer Substances 0.000 title claims description 29
238000002360 preparation method Methods 0.000 title description 11
239000008199 coating composition Substances 0.000 title description 9
239000006185 dispersion Substances 0.000 claims abstract description 52
239000005056 polyisocyanate Substances 0.000 claims abstract description 48
229920001228 polyisocyanate Polymers 0.000 claims abstract description 48
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 33
229920000058 polyacrylate Polymers 0.000 claims abstract description 27
229920005862 polyol Polymers 0.000 claims abstract description 26
150000003077 polyols Chemical class 0.000 claims abstract description 26
229920005989 resin Polymers 0.000 claims abstract description 24
239000011347 resin Substances 0.000 claims abstract description 24
239000007787 solid Substances 0.000 claims abstract description 17
125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
229920001225 polyester resin Polymers 0.000 claims abstract description 14
150000008064 anhydrides Chemical class 0.000 claims abstract description 13
239000004645 polyester resin Substances 0.000 claims abstract description 12
150000002763 monocarboxylic acids Chemical class 0.000 claims abstract description 11
229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
229920000728 polyester Polymers 0.000 claims description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
239000000178 monomer Substances 0.000 claims description 19
150000001735 carboxylic acids Chemical class 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 16
-1 aliphatic alcohols Chemical class 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
150000002148 esters Chemical class 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
229920000877 Melamine resin Polymers 0.000 claims description 6
229920005749 polyurethane resin Polymers 0.000 claims description 5
238000010526 radical polymerization reaction Methods 0.000 claims description 5
235000020354 squash Nutrition 0.000 claims description 5
239000000758 substrate Substances 0.000 claims description 4
150000000000 tetracarboxylic acids Chemical class 0.000 claims description 3
150000003628 tricarboxylic acids Chemical class 0.000 claims description 3
239000004640 Melamine resin Substances 0.000 claims description 2
238000000576 coating method Methods 0.000 abstract description 17
239000000945 filler Substances 0.000 abstract description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 20
235000014113 dietary fatty acids Nutrition 0.000 description 14
239000000194 fatty acid Substances 0.000 description 14
229930195729 fatty acid Natural products 0.000 description 14
150000004665 fatty acids Chemical class 0.000 description 14
238000003756 stirring Methods 0.000 description 13
239000004575 stone Substances 0.000 description 13
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 8
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
239000002981 blocking agent Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000004132 cross linking Methods 0.000 description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 5
239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
239000005058 Isophorone diisocyanate Substances 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
238000009863 impact test Methods 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
150000002513 isocyanates Chemical class 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000004925 Acrylic resin Substances 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
229910000831 Steel Inorganic materials 0.000 description 4
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 4
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
239000011976 maleic acid Substances 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000010959 steel Substances 0.000 description 4
238000003860 storage Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
150000002118 epoxides Chemical class 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
229920000578 graft copolymer Polymers 0.000 description 3
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
238000000034 method Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000003472 neutralizing effect Effects 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229940113165 trimethylolpropane Drugs 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 2
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
125000003504 2-oxazolinyl group Chemical class O1C(=NCC1)* 0.000 description 2
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000005100 correlation spectroscopy Methods 0.000 description 2
IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003822 epoxy resin Substances 0.000 description 2
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical group C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000002209 hydrophobic effect Effects 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
229960002446 octanoic acid Drugs 0.000 description 2
229920002601 oligoester Polymers 0.000 description 2
JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000000312 peanut oil Substances 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229920000647 polyepoxide Polymers 0.000 description 2
239000003505 polymerization initiator Substances 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
229920003009 polyurethane dispersion Polymers 0.000 description 2
230000008569 process Effects 0.000 description 2
CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 1
MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 description 1
POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
VYZKQGGPNIFCLD-UHFFFAOYSA-N 3,3-dimethylhexane-2,2-diol Chemical compound CCCC(C)(C)C(C)(O)O VYZKQGGPNIFCLD-UHFFFAOYSA-N 0.000 description 1
SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
SKKHNUKNMQLBTJ-UHFFFAOYSA-N 3-bicyclo[2.2.1]heptanyl 2-methylprop-2-enoate Chemical compound C1CC2C(OC(=O)C(=C)C)CC1C2 SKKHNUKNMQLBTJ-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
MFKRHJVUCZRDTF-UHFFFAOYSA-N 3-methoxy-3-methylbutan-1-ol Chemical compound COC(C)(C)CCO MFKRHJVUCZRDTF-UHFFFAOYSA-N 0.000 description 1
VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/006—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers provided for in C08G18/00
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/01—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to unsaturated polyesters
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
- C08G18/631—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polyesters and/or polycarbonates
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/8077—Oximes
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Health & Medical Sciences (AREA)
Polymers & Plastics (AREA)
Medicinal Chemistry (AREA)
Wood Science & Technology (AREA)
Life Sciences & Earth Sciences (AREA)
Materials Engineering (AREA)
Engineering & Computer Science (AREA)
Paints Or Removers (AREA)
Polyurethanes Or Polyureas (AREA)
Compositions Of Macromolecular Compounds (AREA)
Application Of Or Painting With Fluid Materials (AREA)
Compounds Of Unknown Constitution (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Adhesives Or Adhesive Processes (AREA)

CA 2280109 1998-08-17 1999-08-12 Compositions de revetements aqueux, preparation et utilisation de ces produits dans la fabrication de vernis-laques au four Expired - Fee Related CA2280109C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE1998137062 DE19837062A1 (de)	1998-08-17	1998-08-17	Wäßrige Beschichtungsmittel, dessen Herstellung und Verwendung für Einbrennlacke
DE1998137063 DE19837063A1 (de)	1998-08-17	1998-08-17	Verwendung einer wäßrigen Bindemittelkombination zur Herstellung von physikalisch trocknenden Überzügen
DE19837062.8		1998-08-17
DE19837063.6		1998-08-17

Publications (2)

Publication Number	Publication Date
CA2280109A1 CA2280109A1 (fr)	2000-02-17
CA2280109C true CA2280109C (fr)	2007-07-24

Family

ID=26048177

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CA 2280108 Abandoned CA2280108A1 (fr)	1998-08-17	1999-08-12	Un procede de preparation de revetements par cuisson physique de dispersions aqueuses
CA 2280109 Expired - Fee Related CA2280109C (fr)	1998-08-17	1999-08-12	Compositions de revetements aqueux, preparation et utilisation de ces produits dans la fabrication de vernis-laques au four

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CA 2280108 Abandoned CA2280108A1 (fr)	1998-08-17	1999-08-12	Un procede de preparation de revetements par cuisson physique de dispersions aqueuses

Country Status (12)

Country	Link
US (2)	US6139918A (fr)
EP (2)	EP0980880B1 (fr)
JP (2)	JP2000080328A (fr)
KR (2)	KR100672869B1 (fr)
AT (2)	ATE282651T1 (fr)
AU (2)	AU743019B2 (fr)
BR (2)	BR9903717A (fr)
CA (2)	CA2280108A1 (fr)
DE (2)	DE59911076D1 (fr)
ES (2)	ES2234190T3 (fr)
PL (1)	PL190131B1 (fr)
PT (2)	PT980881E (fr)

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WO2021094242A1 (fr) *	2019-11-15	2021-05-20	Basf Coatings	Composition de résine à faible teneur en cov, sa résine obtenue et composition de revêtement la comprenant
CN112646459A (zh) *	2020-12-17	2021-04-13	广东花王涂料有限公司	一种木器色漆组合物及木器色漆涂料
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1999
- 1999-08-04 ES ES99115062T patent/ES2234190T3/es not_active Expired - Lifetime
- 1999-08-04 PT PT99115062T patent/PT980881E/pt unknown
- 1999-08-04 DE DE59911076T patent/DE59911076D1/de not_active Expired - Fee Related
- 1999-08-04 EP EP19990115061 patent/EP0980880B1/fr not_active Expired - Lifetime
- 1999-08-04 ES ES99115061T patent/ES2234189T3/es not_active Expired - Lifetime
- 1999-08-04 EP EP19990115062 patent/EP0980881B1/fr not_active Expired - Lifetime
- 1999-08-04 PT PT99115061T patent/PT980880E/pt unknown
- 1999-08-04 AT AT99115061T patent/ATE282651T1/de not_active IP Right Cessation
- 1999-08-04 AT AT99115062T patent/ATE282652T1/de not_active IP Right Cessation
- 1999-08-04 DE DE59911077T patent/DE59911077D1/de not_active Expired - Lifetime
- 1999-08-05 US US09/368,709 patent/US6139918A/en not_active Expired - Fee Related
- 1999-08-11 US US09/371,822 patent/US6380342B2/en not_active Expired - Lifetime
- 1999-08-12 CA CA 2280108 patent/CA2280108A1/fr not_active Abandoned
- 1999-08-12 CA CA 2280109 patent/CA2280109C/fr not_active Expired - Fee Related
- 1999-08-13 PL PL99334913A patent/PL190131B1/pl not_active IP Right Cessation
- 1999-08-16 JP JP22988699A patent/JP2000080328A/ja active Pending
- 1999-08-16 KR KR1019990033569A patent/KR100672869B1/ko not_active Expired - Fee Related
- 1999-08-16 JP JP22988399A patent/JP4579359B2/ja not_active Expired - Fee Related
- 1999-08-16 KR KR1019990033570A patent/KR100672868B1/ko not_active Expired - Fee Related
- 1999-08-17 BR BR9903717A patent/BR9903717A/pt not_active IP Right Cessation
- 1999-08-17 BR BR9903723A patent/BR9903723A/pt not_active Application Discontinuation
- 1999-08-17 AU AU44530/99A patent/AU743019B2/en not_active Ceased
- 1999-08-17 AU AU44528/99A patent/AU755832B2/en not_active Ceased

Also Published As

Publication number	Publication date
PT980881E (pt)	2005-03-31
BR9903723A (pt)	2000-09-12
KR20000017316A (ko)	2000-03-25
JP2000080328A (ja)	2000-03-21
AU4452899A (en)	2000-03-09
EP0980881B1 (fr)	2004-11-17
US20020002237A1 (en)	2002-01-03
EP0980880A1 (fr)	2000-02-23
ES2234189T3 (es)	2005-06-16
US6380342B2 (en)	2002-04-30
DE59911077D1 (de)	2004-12-23
KR100672868B1 (ko)	2007-01-24
ATE282652T1 (de)	2004-12-15
CA2280108A1 (fr)	2000-02-17
EP0980880B1 (fr)	2004-11-17
AU755832B2 (en)	2002-12-19
JP2000063482A (ja)	2000-02-29
JP4579359B2 (ja)	2010-11-10
AU743019B2 (en)	2002-01-17
ATE282651T1 (de)	2004-12-15
DE59911076D1 (de)	2004-12-23
EP0980881A1 (fr)	2000-02-23
ES2234190T3 (es)	2005-06-16
PT980880E (pt)	2005-03-31
BR9903717A (pt)	2000-09-12
US6139918A (en)	2000-10-31
KR100672869B1 (ko)	2007-01-24
PL190131B1 (pl)	2005-11-30
KR20000017315A (ko)	2000-03-25
CA2280109A1 (fr)	2000-02-17
AU4453099A (en)	2000-03-09
PL334913A1 (en)	2000-02-28

Legal Events

Date	Code	Title	Description
2004-06-22	EEER	Examination request
2008-08-12	MKLA	Lapsed

Publication	Publication Date	Title
CA2280109C (fr)	2007-07-24	Compositions de revetements aqueux, preparation et utilisation de ces produits dans la fabrication de vernis-laques au four
JP4906218B2 (ja)	2012-03-28	水系架橋性バインダー組成物および該バインダー組成物を含むコーティング、ラッカーまたはシーリング組成物
US5391620A (en)	1995-02-21	Composition suitable as a rheology-influencing agent, a method for its preparation and its use in coating media
CA2113964A1 (fr)	1994-07-22	Polymere hybride dispersible dans l'eau
US6406753B2 (en)	2002-06-18	Aqueous coating composition
CA2401213A1 (fr)	2001-09-07	Agents de revetement aqueux pour vernis a cuire riches en matiere solide et leur utilisation
US6521700B1 (en)	2003-02-18	Aqueous coating composition
US5807924A (en)	1998-09-15	Coating media and a process for producing multi-layer coatings
US7022760B2 (en)	2006-04-04	Crosslinkable binder dispersions
EP0962507B1 (fr)	2004-08-04	Liants pour compositions de revètement
WO2023166133A1 (fr)	2023-09-07	Dispersion hybride polyester-polyuréthane-poly(méth)acrylique
US7022778B2 (en)	2006-04-04	High solid coating compositions
DE19837062A1 (de)	2000-02-24	Wäßrige Beschichtungsmittel, dessen Herstellung und Verwendung für Einbrennlacke
MXPA99007590A (en)	2000-06-05	Aqueous recovery product, its preparation and use for drying enamels
MXPA99007588A (en)	2000-06-05	Use of an aqueous agglutinant combination for the preparation of fis drying layers